Semisynthesis of new D-seco-C-nor-taxane derivatives containing a polyfunctionalized furanosyl or cyclopentenyl or cyclopentyl C-ring.
The synthesis of new D-seco-C-nor-taxane derivatives in which the D-ring has been deleted and the C-ring has been transformed into a new pentatomic ring, i.e., the polyfunctionalized tetrahydrofuranosyl and cyclopentenyl or cyclopentyl ring, was performed starting from baccatin III derivatives. The synthetic strategy adopted took advantage of the oxetane ring opening and disconnection of the C4-C5 bond, followed by an intramolecular condensation. The formation of furanosyl or cyclopentyl rings is strictly dependent on the presence of unprotected or protected oxygen at C-7 in the starting material. The reactions proceeded with good diastereoselectivity with control of the stereochemistry of one or two stereocenters.
Gelmi
Maria Luisa
ML
Istituto di Chimica Organica A. Marchesini Facoltà di Farmacia, Università degli Studi di Milano, via Venezian 21, 20133, Milano, Italy. marialuisa.gelmi@unimi.it
Nava
Donatella
D
Leone
Samantha
S
Pellegrino
Sara
S
Baldelli
Eleonora
E
Zunino
Franco
F
Cappelletti
Graziella
G
Cartelli
Daniele
D
Fontana
Gabriele
G
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002460:Cell Line; D003517:Cyclopentanes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D013237:Stereoisomerism; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity
D001952:Bridged-Ring Compounds; D003517:Cyclopentanes; D005663:Furans; D043823:Taxoids; C080625:taxane; C039281:furan